Mickey Drexler doesn’t like to wait for things to happen. His storied retail career, with executive roles at companies like Ann Taylor, Gap Inc., and J.Crew, was defined by a bullish leadership style and a move-fast, get-results attitude that helped catapult those businesses into American retail mammoths. Old Navy, which he launched during his time at Gap Inc. in 1994 in about 18 months, became the fastest retailer to reach $1 billion in sales in four years.
But when he joined Alex Mill as chairman in 2019 — the New York brand founded by his son, Alex, in 2012 — Mickey had to be patient. “We put the time in and the work. Now, I feel very good about where we are,” he says. “But you never can relax in this business. Because there’s always the next season, the next year.”
Alex Mill started with a simple premise — a better men’s button-down — and has grown to a full-fledged men’s and women’s fashion brand with a reputation for colorful knits and natural materials. If you blur your eyes, you might think you’re looking at J.Crew’s website as you scroll. But the secret sauce that separates Alex Mill from Mickey’s past endeavors is in the details and behind the scenes. Mickey, when he officially came on board as chairman (reporting to Alex), did so on the basis that he wouldn’t have oversight from investors — it would just be him and his son, plus Alex Mill’s creative director, Somsack Sikhounmuong, who worked with Mickey at J.Crew before he joined Alex Mill, at the helm.
“I joined [in 2019] because I frankly didn’t want to have investors anymore,” Mickey says. “Small is the new big. That’s what we always say. And actually, I love small, because big companies today are bureaucratic. There’s an ivory tower,” he says. He had closed out his time as the CEO of J.Crew in 2017 and spent two years as J.Crew’s executive chairman, as well as on the boards of other brands, including a stint as chairman of Outdoor Voices. “And if you want something done, you have to go through layers upon layers. And even then, you don’t get an answer.”
We’re sitting in a conference room at Alex Mill’s shabby-chic SoHo offices. Alex, Mickey, and Sikhounmuong, who also joined in 2019, have gathered to discuss the brand’s launch of a mini tote bag and ballet flats. It’s the next evolution of what Mickey joined to do, which was start the brand’s womenswear business after it spent the first five years dealing in men’s clothing (the first signal that there was an appetite for womenswear was when Goop bought its men’s shirts for its women’s store in 2015.) The ballet shoes are made in Florence and come in seven colors. The Perfect Little tote launches on March 10 and expands the tote category, which has become the brand’s bestseller.
It’s the Drexlers’ first joint interview discussing the business, but Mickey does most of the talking. I make sure to ask about these new products, but we don’t stay on them long. Mickey is the type of interview that makes a PR person squirm. At 81, he’s at the no-fucks stage of his career, and it’s clear he doesn’t play when it comes to Alex Mill.
He’s also so full of retail lessons that, when he lays them out, makes you wonder what could be so hard about running a solid business. “For me, it’s the most gratifying job I’ve had in the industry,” he says of the Alex Mill gig. Mickey’s also sure to point out the challenges of operating without the resources of a multi-billion-dollar brand. “A small business without all those people is as much good news as it is bad news.”
Mickey’s vision, which his son says aligns with his founding stance for Alex Mill, isn’t radical. It’s to perfect style and taste with quality materials at a good value, all supported by a savvy marketing strategy. The story Alex tells about deciding to launch the brand is a familiar one, as far as the 2010s direct-to-consumer era of brand launches goes: “I couldn’t find the perfect shirt with the right fabric, the right fit, the right details,” he says. The difference was that Alex didn’t saddle the company with venture capital. Industry connections might have helped. When Alex set out to launch his brand, he was working for his dad’s close friend and Theory founder Andrew Rosen, on his former brand, Gryphon New York.
But when I ask how Alex Mill tempers its growth to keep all of this in balance — when does the performance marketing faucet turn on for customer acquisition, for instance — Mickey refutes the idea. “We don’t want to be so small,” he says. The brand is set to reach profitability this year and has more than doubled sales year over year.
Alex Mill’s team consists of about 30 people. During my visit, Mickey walks around the desks, asking the social team to show me the upcoming Tote Club campaign they’re working on, which invites notable New Yorkers to share what’s in their Alex Mill bags. “I’ve been fortunate with the team; they work hard, and I love working with them. I think I’m much less difficult now,” Mickey says.
He asks the group whether they agree that he’s less difficult than he might have been in the past, while Sikhounmuong jokes about sometimes serving as a mediator between father and son. Alex, for his part, says he loves working with his dad. “Or they’re used to me,” Mickey shrugs.
Growth at all costs is often where fashion brands lose their way. The main culprits are cut corners, private equity, and non-merchant types getting control of merchant-based retailers. Alex Mill’s counter to this path is to be almost inconceivably human as a business. The leadership team listens to feedback from employees and customers, and they answer the phone and emails. They don’t use AI design tools, something Mickey has gotten into arguments with industry peers about.
“AI doesn’t have emotion. It doesn’t have a point of view on merchandising, and it’ll copy everything, whatever around,” he says. Mickey points to the success of the Alex Mill totes, which can be personalized with bold block initials in hand-painted colors. “Creativity is the key to success, along with quality. It’s what people want today: real stuff.”
This human approach is what guides Alex Mill’s collaborations. When Saks went under, Mickey spoke to the owner of a sunglasses brand who was worried about what would happen to her business. He told her to stop sending any shipments to Saks; Alex Mill would sell the glasses instead. The brand has a small area of its site where it collaborates with brands that fit its aesthetic, but instead of an actual collab, it’s really just Alex Mill selling the pieces — sunglasses, jewelry from Lié Jewelry, loafers from an Italian shop — on its site under an “In Great Company” section. Mickey considers it curation over collaboration: “Everything you do in this business needs to be curated.”
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The biggest corner that gets cut is typically quality: more brands like Gap and J.Crew are now investing back in 100% cotton sweaters and real linen blends, in response to a growing customer backlash to synthetics. It’s where the brand has been this whole time. Its sweaters are 100% cashmere; T-shirts are 100% cotton. “Some of these suppliers we’ve worked with for many years, and we have longstanding relationships with,” Sikhounmuong says. He says last year’s tariffs posed a challenge as costs rose. “Every little detail is so important — the hand feel of the fabric, the buttons, the trims.” The restraint, too. Sikhounmuong and Alex point out that it’s easier to keep quality in check when they’re designing five styles of shirts instead of 100. “The amount of time we’re able to devote to each shirt is so much more,” says Sikhounmuong. “So we really make sure we do a good job at it.”
Category launches, like the flat and the mini tote, are highly considered and don’t materialize too often, the team says. The focus is more about getting the word out about the brand. New stores are coming to US locations like LA’s Brentwood Market and Nantucket, while the team is eyeing London for its first international outpost.
The hardest part is cutting through the noise when the last 15 years have seen a deluge of new clothing brands on the market that promise to be better than the ones that came before. Mickey’s way of working to ensure the brand lasts is to show that there’s no task too small. He’ll get on Instagram for a video about the brand’s new mini tote, and host Monday morning “Weekend Updates” with the team to hear what’s taken place in the world of fashion since the Friday before.
“I’m not an executive. I’m a worker, and I’ve always been a worker. And you can’t have an ego if you’re going to report to your son.”
